CN101492348A - Method for producing 1-adamantane ethanol - Google Patents
Method for producing 1-adamantane ethanol Download PDFInfo
- Publication number
- CN101492348A CN101492348A CNA2009100584350A CN200910058435A CN101492348A CN 101492348 A CN101492348 A CN 101492348A CN A2009100584350 A CNA2009100584350 A CN A2009100584350A CN 200910058435 A CN200910058435 A CN 200910058435A CN 101492348 A CN101492348 A CN 101492348A
- Authority
- CN
- China
- Prior art keywords
- diamantane
- adamantanol
- reaction
- bromination
- bromine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- ZBIDZPHRNBZTLT-UHFFFAOYSA-N 2-(1-adamantyl)ethanol Chemical compound C1C(C2)CC3CC2CC1(CCO)C3 ZBIDZPHRNBZTLT-UHFFFAOYSA-N 0.000 title 1
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000005893 bromination reaction Methods 0.000 claims abstract description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 15
- 230000031709 bromination Effects 0.000 claims abstract description 14
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 230000002140 halogenating effect Effects 0.000 claims abstract description 4
- ZICQBHNGXDOVJF-UHFFFAOYSA-N diamantane Chemical compound C1C2C3CC(C4)CC2C2C4C3CC1C2 ZICQBHNGXDOVJF-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 11
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 abstract 8
- 239000000047 product Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for producing a 1-adamantanol product which is prepared by subjecting adamantane to bromination reaction and hydrolysis reaction. Bromine is used as a halogenating agent, and the dosage is one to ten times of the adamantane in mole number. A is used as a bromination catalyst, and the dosage is 0.5 percent to 5 percent of the weight of the adamantane. The temperature of the bromination reaction is 0 DEG C to 100 DEG C, and the reaction pressure is normal pressure. The invention is characterized in that the hydrolysis temperature of 1-bromine adamantane is 100 DEG C to 150 DEG C, and the reaction pressure is 0-3atm. The purity of the 1-adamantanol obtained by the invention is more than or equal to 99.5 percent, and the yield is more than 95 percent.
Description
One, technical field
The present invention relates to the production of 1-adamantanol product, provide a kind of diamantane to produce in the 1-adamantanol product process especially through bromination, hydrolysis reaction, produce 1-bromine diamantane by catalytic bromination, and method low-cost, high purity 1-adamantanol product is produced in hydrolysis under certain pressure.
Two, background technology
1-adamantanol product is widely used at medicine, electronic material and cosmetic field as a kind of important fine chemical product.1-adamantanol product is to form through bromination, hydrolysis reaction from diamantane.There was the not thorough or excessive bromination of bromination in the past in the production of this product, caused product quality poor, the aftertreatment complexity; The 1-adamantanol poor quality of producing, yield is low, and the manufacturing cost height is difficult to satisfy the derived product needs.
The object of the present invention is to provide the method for the synthetic 1-adamantanol of a kind of high yield, make bromination catalyst by using catalyst A, can synthesize 1-bromine diamantane through catalytic bromination by diamantane, and low-cost, high purity 1-adamantanol product are produced in hydrolysis under certain pressure.
Three, summary of the invention
The invention provides a kind of method of the 1-of production adamantanol product, form through bromination, hydrolysis reaction by diamantane; With the bromine is halogenating agent, and its consumption is 1～10 times of diamantane mole number, and optimum amount is 1～2 times of diamantane mole number; Make bromination catalyst with A, its consumption is 0.5～5% of a diamantane weight, and optimum amount is 1～2% of a diamantane weight; The bromination reaction temperature is 0～100 ℃, is good with 50～70 ℃, and reaction pressure is a normal pressure; It is characterized in that: 1-bromine diamantane hydrolysis temperature is 100～150 ℃, is good with 120～130 ℃ of hydrolysis temperatures, and reaction pressure is 0～3atm.
Four, embodiment
Give further instruction below by example to the present invention.
Embodiment 1: synthetic 1-bromine diamantane
Add diamantane 200kg in the reactor of clean dried, catalyst A 2kg is pressed into header tank with the 470kg bromine.Slowly bromine is added dropwise to reactor, reaction is 3 hours under 60 ℃ of conditions.After sampling analysis was qualified, bromine was reclaimed in distillation.Concentrated solution adds sig water and neutralizes, and continues to stir cooling, then with the material centrifugation, gets 1-bromine diamantane 318kg, content 98.5%, yield 99%.
Embodiment 2: synthetic 1-adamantanol product
In clean reactor, add 350 liters in 1-bromine diamantane 350kg, water, be warming up to 120 ℃, 1.5atm pressure, hydrolysis reaction 6 hours.Product is separated out in cooling then, gets 1-adamantanol crude product, and crude product gets elaboration 1-adamantanol product 238kg, content 99.7%, yield 97.4% behind decolouring, recrystallization.
Embodiment 3: synthetic 1-adamantanol product
In clean reactor, add 350 liters in 1-bromine diamantane 350kg, water, be warming up to 130 ℃, 2atm pressure, hydrolysis reaction 5 hours.Product is separated out in cooling then, gets 1-adamantanol crude product, and crude product gets elaboration 1-adamantanol 237kg, content 99.6%, yield 96.9% behind decolouring, recrystallization.
Comparative example 1: synthetic 1-bromine diamantane
In the reactor of clean dried, add diamantane 200kg, the 470kg bromine is pressed into header tank.Slowly bromine is added dropwise to reactor, reaction is 3 hours under 60 ℃ of conditions.After sampling analysis is qualified, add sig water and neutralize, continue to stir cooling, then with the material centrifugation, get 1-bromine diamantane 220kg, content 95.5%, yield 66.4%.
Claims (6)
1. a method of producing 1-adamantanol product is formed through bromination, hydrolysis reaction by diamantane; With the bromine is halogenating agent, and its consumption is 1～10 times of diamantane mole number; Make bromination catalyst with A, its consumption is 0.5～5% of a diamantane weight; The bromination reaction temperature is 0～100 ℃, and reaction pressure is a normal pressure; It is characterized in that: 1-bromine diamantane hydrolysis temperature is 100～150 ℃, and reaction pressure is 0～3atm.
2. by the method for the described production of claim 1 1-adamantanol product, it is characterized in that: form through bromination, hydrolysis reaction by diamantane.
3. by the method for claim 1 or 2 described production 1-adamantanol products, it is characterized in that: make bromination catalyst with A, its consumption is 0.5～5% of a diamantane weight
4. by the method for claim 1 or 2 described production 1-adamantanol products, it is characterized in that: be halogenating agent with the bromine, its consumption is 1～10 times of diamantane mole number.
5. by the method for claim 1 or 2 described production 1-adamantanol products, it is characterized in that: the bromination reaction temperature is 0～100 ℃, and reaction pressure is a normal pressure.
6. by the method for claim 1 or 2 described production 1-adamantanol products, it is characterized in that: 1-bromine diamantane hydrolysis temperature is 100～150 ℃, and reaction pressure is 0～3atm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009100584350A CN101492348A (en) | 2009-02-26 | 2009-02-26 | Method for producing 1-adamantane ethanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009100584350A CN101492348A (en) | 2009-02-26 | 2009-02-26 | Method for producing 1-adamantane ethanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101492348A true CN101492348A (en) | 2009-07-29 |
Family
ID=40923162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2009100584350A Pending CN101492348A (en) | 2009-02-26 | 2009-02-26 | Method for producing 1-adamantane ethanol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101492348A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102127583A (en) * | 2010-01-19 | 2011-07-20 | 上海博康精细化工有限公司 | Method for preparing anti-para amino adamantanol |
| CN106631690A (en) * | 2016-11-11 | 2017-05-10 | 中节能万润股份有限公司 | Preparation method of 1-adamantanol |
| CN114127241A (en) * | 2019-07-19 | 2022-03-01 | 高砂香料工业株式会社 | Fragrance composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1660738A (en) * | 2004-12-24 | 2005-08-31 | 中国科学院广州化学研究所 | Method for synthesizing 3,5-dibasic-1-adamantine alcohol |
-
2009
- 2009-02-26 CN CNA2009100584350A patent/CN101492348A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1660738A (en) * | 2004-12-24 | 2005-08-31 | 中国科学院广州化学研究所 | Method for synthesizing 3,5-dibasic-1-adamantine alcohol |
Non-Patent Citations (1)
| Title |
|---|
| 彭贵存: "金刚烷及其衍生物", 《河北师范大学学报( 自然科学版)》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102127583A (en) * | 2010-01-19 | 2011-07-20 | 上海博康精细化工有限公司 | Method for preparing anti-para amino adamantanol |
| CN106631690A (en) * | 2016-11-11 | 2017-05-10 | 中节能万润股份有限公司 | Preparation method of 1-adamantanol |
| CN114127241A (en) * | 2019-07-19 | 2022-03-01 | 高砂香料工业株式会社 | Fragrance composition |
| CN114127241B (en) * | 2019-07-19 | 2024-03-08 | 高砂香料工业株式会社 | Perfume composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102030646B (en) | Direct transformation process of ethyl levulinate by hydrolysis of cellulose materials | |
| CN110862310B (en) | Synthesis method of cyclopropyl methyl ketone | |
| WO2007089527B1 (en) | Method of forming a dianhydrosugar alcohol | |
| CN105968149A (en) | Preparation method of beta-arbutin | |
| CN101492348A (en) | Method for producing 1-adamantane ethanol | |
| CN101157615A (en) | Method for producing plasticizer phthalic acid dinonyl | |
| CN102020543B (en) | Method for producing 9-fluorenone | |
| CN106431911B (en) | Preparation and purification method of 4-felbinac | |
| CN108530301B (en) | Synthetic method of 2,4, 6-trifluorobenzylamine | |
| CN101468981A (en) | Preparation technique of lactide | |
| MX2011009028A (en) | Process for producing 3,4' dihydroxybenzophenone as an intermediate for producing 3,4' diacetoxybenzophenone. | |
| CN104292113A (en) | Preparation method of 3-chloro-4-fluoroaniline | |
| CN104109114B (en) | A kind of preparation method of the 2-ethoxy pyridine of high-efficiency environment friendly | |
| CN102295623A (en) | Method for preparing N-acetylmorpholine by using ketene | |
| CN110845440B (en) | Method for preparing 2-mercaptobenzothiazole | |
| CN102976888A (en) | Synthesizing method of p-dichlorobenzene | |
| CN107892707B (en) | A kind of synthetic method of vidarabine | |
| CN115784861B (en) | A method for producing trichloroacetone using continuous microchannel technology | |
| CN102942479A (en) | Method for preparing propylene glycol methyl ether acetate through two-step coupling reaction | |
| CN105622449A (en) | Process for synthesizing paracetamol | |
| CN111039917A (en) | Preparation method of 1, 4-cyclohexanedione mono-ketal | |
| CN109400468B (en) | Preparation method of L-dibenzoyl dimethyl tartrate | |
| CN101531583A (en) | Method for the synthesis of alpha-bromoadamantane acetic acid at high yield | |
| CN102659626B (en) | Method for reducing waste residues of 4-Bromomethyl-2-cyanobiphenyl | |
| CN107417533B (en) | Dimethyl isophthalate and process for producing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20090729 |
|
| C10 | Entry into substantive examination | ||
| CI01 | Publication of corrected invention patent application |
Correction item: deemed withdrawal of patent application after publication Correct: The revocation of the patent application shall be deemed to be withdrawn False: The withdrawal of the patent application shall be deemed to be withdrawn Number: 01 Volume: 29 |
|
| ERR | Gazette correction |
Free format text: CORRECT: PATENT APPLICATION AFTER PUBLICATION DEEMED WITHDRAWAL; FROM: PATENT APPLICATION AFTER PUBLICATION DEEMED WITHDRAWAL TO: REVOCATION PATENT APPLICATION AFTER PUBLICATION DEEMED WITHDRAWAL |
|
| SE01 | Entry into force of request for substantive examination | ||
| DD01 | Delivery of document by public notice |
Addressee: Luo Xinping Document name: Notification of Passing Examination on Formalities |
|
| ASS | Succession or assignment of patent right |
Owner name: YIBIN KAISITE PHARMACEUTICAL CHEMICAL CO., LTD. Free format text: FORMER OWNER: LUZHOU WANLIAN CHEMICAL CO., LTD. Effective date: 20140306 |
|
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 646000 LUZHOU, SICHUAN PROVINCE TO: 644200 YIBIN, SICHUAN PROVINCE |
|
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20140306 Address after: Yangchun City of Sichuan province Yibin Industrial Park 644200 Jiangan Applicant after: YIBIN CHEMIST PHARMACHEM CO.,LTD. Address before: 646000 hundred towns, Luzhou, Sichuan, Luxian County Applicant before: LUZHOU WANLIAN CHEMICAL Co.,Ltd. |
|
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20090729 |